Aurone

File:Aurones numb.svg

Aurone forms the core for a family of derivatives which are known collectively as aurones. Aurones are plant flavonoids that provide yellow color to the flowers of some popular ornamental plants, such as snapdragon and cosmos.{{cite journal | doi = 10.1016/S0014-5793(01)02529-7 | pmid = 11418122 | year = 2001 | last1 = Nakayama | first1 = T | last2 = Sato | first2 = T | last3 = Fukui | first3 = Y | last4 = Yonekura-Sakakibara | first4 = K | last5 = Hayashi | first5 = H | last6 = Tanaka | first6 = Y | last7 = Kusumi | first7 = T | last8 = Nishino | first8 = T | title = Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration | volume = 499 | issue = 1–2 | pages = 107–11 | journal = FEBS Letters | doi-access = }} Aurones including 4'-chloro-2-hydroxyaurone (C₁₅H₁₁O₃Cl) and 4'-chloroaurone (C₁₅H₉O₂Cl) can also be found in the brown alga Spatoglossum variabile.{{cite journal|doi=10.1248/cpb.49.105 |pmid=11201212 |last1=Atta-Ur-Rahman | year=2001 |last2=Choudhary |first2=MI |last3=Hayat |first3=S |last4=Khan |first4=AM |last5=Ahmed |first5=A |title=Two new aurones from marine brown alga Spatoglossum variabile |volume=49 |issue=1 |pages=105–7 |journal=Chemical & Pharmaceutical Bulletin|doi-access=free }}

Most aurones are in a (Z)-configuration, which is the more stable configuration according to Austin Model 1 computation. But there are also some in the (E)-configurations such as (E)-3'-O-β-d-glucopyranosyl-4,5,6,4'-tetrahydroxy-7,2'-dimethoxyaurone, found in Gomphrena agrestis.{{cite journal | pmid = 15813368 | url = http://www.znaturforsch.com/ac/v59c/s59c0499.pdf | year = 2004 | last1 = Ferreira | first1 = EO | last2 = Salvador | first2 = MJ | last3 = Pral | first3 = EM | last4 = Alfieri | first4 = SC | last5 = Ito | first5 = IY | last6 = Dias | first6 = DA | title = A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity | volume = 59 | issue = 7–8 | pages = 499–505 | journal = Zeitschrift für Naturforschung C | doi = 10.1515/znc-2004-7-808 | s2cid = 15589214 }}

Aurones are biosynthesized starting from coumaryl-CoA.{{cite journal |journal =Molecular Plant |volume=3 |year=2010 |pages=2–20 |doi= 10.1093/mp/ssp106 |title=Phenylpropanoid Biosynthesis |author=Vogt, T. |pmid=20035037|doi-access=free }} Aureusidin synthase catalyzes the creation of aurones from chalcones through hydroxylation and oxidative cyclization.

Some aurone derivatives possess antifungal properties{{Cite journal|last1=Sutton|first1=Caleb L.|last2=Taylor|first2=Zachary E.|last3=Farone|first3=Mary B.|last4=Handy|first4=Scott T.|date=2017-02-15|title=Antifungal activity of substituted aurones|journal=Bioorganic & Medicinal Chemistry Letters|volume=27|issue=4|pages=901–903|doi=10.1016/j.bmcl.2017.01.012|pmid=28094180}} and analogy with flavonoids suggests that aurones could have other biological properties.{{cite journal | doi = 10.3390/30300088 | title = Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones | year = 1998 | last1 = Villemin | first1 = Didier | last2 = Martin | first2 = Benoit | last3 = Bar | first3 = Nathalie | journal = Molecules | volume = 3 | pages = 88 | issue = 8| doi-access = free }}

• Aureusidin
• Hispidol (6,4'-dihydroxyaurone)[http://metabolomics.jp/wiki/FL1A1ANS0001 Hispidol on metabolomics.jp]
• Leptosidin
• Sulfuretin (6,3',4'-trihydroxyaurone)
• 4,5,6-Trihydroxyaurone

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{{flavonoids}}

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